Asymmetric total synthesis of hedyosumin E aglycon, 7,10-epoxyhedyosminolide and ent-zedolactone A

2016 ◽  
Vol 14 (45) ◽  
pp. 10581-10584 ◽  
Author(s):  
Xuan Wang ◽  
Wang-Bin Sun ◽  
Jian-Ping Zou ◽  
Guo-Qiang Lin ◽  
Bing-Feng Sun
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses ◽  
First Time

The asymmetric total syntheses of hedyosumin E aglycon, 7,10-epoxyhedyosminolide and ent-zedolactone A were realized, with the first two being achieved for the first time.

scholarly journals Strategies and Efforts towards the Total Synthesis of Palhinine Alkaloids

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4211
Author(s):  
Yu-Yan Liang ◽  
Shi-Chao Lu ◽  
Ya-Ling Gong ◽  
Shu Xu
Keyword(s):  
Total Synthesis ◽  
Review Article ◽  
Research Groups ◽  
Asymmetric Total Synthesis ◽  
Carbon Cage ◽  
Total Syntheses ◽  
The Past ◽  
Lycopodium Alkaloids

The palhinine family of Lycopodium alkaloids were first reported in 2010, which feature an intriguing isotwistane carbon cage and a nine-membered azonane ring. It is noteworthy that the tetracyclic 5/6/6/9 skeleton was unprecedented in Lycopodium alkaloids before their seminal discovery. Over the past decade, extensive synthetic efforts stemming from seven research groups have resulted in two racemic total syntheses to date. This review article takes the opportunity to survey these efforts and achievements so as to promote further research towards the asymmetric total synthesis of palhinine alkaloids.

Asymmetric total syntheses of naturally occurring α,β-enone-containing RALs, L-783290 and L-783277 through intramolecular base-mediated macrolactonization reaction

2020 ◽  
Vol 18 (12) ◽  
pp. 2331-2345
Author(s):  
Joy Chakraborty ◽  
Ankan Ghosh ◽  
Samik Nanda
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses ◽  
Naturally Occurring

Asymmetric total synthesis of two naturally occurring α,β-enone containing RALs, L-783290 and L-783277 is described in this article.

Asymmetric total synthesis of talienbisflavan A

2018 ◽  
Vol 16 (4) ◽  
pp. 585-592 ◽  
Author(s):  
Deng-Ming Huang ◽  
Hui-Jing Li ◽  
Jun-Hu Wang ◽  
Yan-Chao Wu
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis ◽  
Facile Synthesis ◽  
Total Syntheses ◽  
Key Steps

The first asymmetric total syntheses of talienbisflavan A and bis-8,8′-epicatechinylmethane as well as a facile synthesis of bis-8,8′-catechinylmethane has been accomplished from readily available starting materials by using a newly developed direct regioselective methylenation of catechin derivatives as one of the key steps.

Asymmetric total synthesis of cephanolide B

2021 ◽  
Author(s):  
Hongyuan Zhang ◽  
Haibing He ◽  
Shuanhu Gao
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Asymmetric Total Synthesis ◽  
First Time

The asymmetric synthesis of cephanolide B, a complex C18 Cephalotaxus dinorditerpenoid, is presented for the first time.

Total synthesis of nafuredin B

2020 ◽  
Vol 18 (12) ◽  
pp. 2346-2359
Author(s):  
Gour Hari Mandal ◽  
Dhiman Saha ◽  
Rajib Kumar Goswami
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis ◽  
Convergent Approach ◽  
First Time

Asymmetric total synthesis of nafuredin B has been achieved for the first time following a convergent approach.

scholarly journals Recent progress in organocatalytic asymmetric total syntheses of complex indole alkaloids

2017 ◽  
Vol 4 (3) ◽  
pp. 381-396 ◽  
Author(s):  
Jin Song ◽  
Dian-Feng Chen ◽  
Liu-Zhu Gong
Keyword(s):  
Total Synthesis ◽  
Multiple Bond ◽  
Indole Alkaloids ◽  
Cascade Reactions ◽  
Pharmaceutical Products ◽  
Chiral Molecules ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses ◽  
Asymmetric Organocatalysis ◽  
Optically Pure

Abstract Indole and its structural analogues have been frequently found in numerous alkaloids, pharmaceutical products and related materials. The enantioselective construction of these structures allows efficient total synthesis of optically pure indole alkaloids, and hence has received worldwide interest. In the past decade, asymmetric organocatalysis has been recognized as one of the most powerful strategies to create chiral molecules with high levels of stereoselectivity. In particular, organocatalytic asymmetric cascade reactions often occur with multiple bond-breaking and forming events simultaneously or sequentially, leading to the appearance of various straightforward approaches to access core structures for asymmetric total synthesis. This review will summarize recent applications of asymmetric organocatalysis in the enantioselective synthesis of indole alkaloids.

Asymmetric total synthesis of paecilomycin E, 10′-epi-paecilomycin E and 6′-epi-cochliomycin C

2014 ◽  
Vol 12 (41) ◽  
pp. 8257-8274 ◽  
Author(s):  
Pratik Pal ◽  
Nandan Jana ◽  
Samik Nanda
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses

The asymmetric total syntheses of paecilomycin E and its stereoisomers have been disclosed by employing the late stage Mitsunobu macrolactonization reaction.

scholarly journals 4-Step Total Synthesis of (−)-Pavidolide B

2020 ◽  
Author(s):  
Yaoqiu Zhu ◽  
Elkin L. Romero ◽  
Kolluru Srinivas ◽  
Elizabeth Noriega
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Michael Addition ◽  
Cascade Reaction ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses ◽  
One Step

(−)-Pavidolide B is a complex tetracyclic diterpenoid with seven contiguous stereocenters, and classical total syntheses have recently been reported. In this work, an annulation strategy of carbanion cascade reaction is formulated for accomplishing an asymmetric total synthesis of (−)-pavidolide B in just 4 linear steps. The key reaction is a tandem intramolecular Michael addition, which constructs two 5-membered rings and five stereocenters in a highly selective fashion in one step. This work represents one of the most efficient cases of total synthesis and demonstrates that synthetic access to complex therapeutic natural product can be greatly simplified.

scholarly journals 4-Step Total Synthesis of (−)-Pavidolide B

2020 ◽  
Author(s):  
Yaoqiu Zhu ◽  
Elkin L. Romero ◽  
Kolluru Srinivas ◽  
Elizabeth Noriega
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Michael Addition ◽  
Cascade Reaction ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses ◽  
One Step

(−)-Pavidolide B is a complex tetracyclic diterpenoid with seven contiguous stereocenters, and classical total syntheses have recently been reported. In this work, an annulation strategy of carbanion cascade reaction is formulated for accomplishing an asymmetric total synthesis of (−)-pavidolide B in just 4 linear steps. The key reaction is a tandem intramolecular Michael addition, which constructs two 5-membered rings and five stereocenters in a highly selective fashion in one step. This work represents one of the most efficient cases of total synthesis and demonstrates that synthetic access to complex therapeutic natural product can be greatly simplified.

The Total Synthesis of Rhabdastrellic Acid A

2018 ◽  
Author(s):  
Yaroslav Boyko ◽  
Christopher Huck ◽  
David Sarlah
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Side Chains ◽  
General Strategy ◽  
Modular Approach ◽  
Linear Sequence ◽  
Generating Sequence ◽  
First Time

<div>The first total synthesis of rhabdastrellic acid A, a highly cytotoxic isomalabaricane triterpenoid, has been accomplished in a linear sequence of 14 steps from commercial geranylacetone. The prominently strained <i>trans-syn-trans</i>-perhydrobenz[<i>e</i>]indene core characteristic of the isomalabaricanes is efficiently accessed in a selective manner for the first time through a rapid, complexity-generating sequence incorporating a reductive radical polyene cyclization, an unprecedented oxidative Rautenstrauch cycloisomerization, and umpolung 𝛼-substitution of a <i>p</i>-toluenesulfonylhydrazone with in situ reductive transposition. A late-stage cross-coupling in concert with a modular approach to polyunsaturated side chains renders this a general strategy for the synthesis of numerous family members of these synthetically challenging and hitherto inaccessible marine triterpenoids.</div>

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